4,5-Imidazoledicarboxylic acid Chemical Properties

Melting point:

280-285 °C (dec.) (lit.)

Boiling point:

280.29°C (rough estimate)

bulk density

650-660kg/m3

Density 

1,749 g/cm³

refractive index 

1.4800 (estimate)

storage temp. 

Store below +30°C.

solubility 

0.5g/l

pka

3.59±0.10(Predicted)

form 

Fine Crystalline Powder

color 

Light yellow to yellow-brown

PH

3.7 (0.5g/l, H2O, 20℃)

Water Solubility 

0.5g/L(20 ºC)

BRN 

147774

InChIKey

ZEVWQFWTGHFIDH-UHFFFAOYSA-N

CAS DataBase Reference

570-22-9(CAS DataBase Reference)

NIST Chemistry Reference

4,5-Imidazole dicarboxylic acid(570-22-9)

EPA Substance Registry System

1H-Imidazole-4,5-dicarboxylic acid (570-22-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

NI4760000

Autoignition Temperature

430°C

TSCA 

Yes

HS Code 

29332990

MSDS

• Language:English Provider:4,5-Imidazoledicarboxylic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4,5-Imidazoledicarboxylic acid Usage And Synthesis

Chemical Properties

light yellow to yellow-brown fine cryst. powder

Uses

4,5-Imidazoledicarboxylic Acid is an intermediate used in the synthesis of N-substituted cyclic imides with anticancer and anti-inflammatory activities. it is also used to prepare imidazolecarboxamide derivatives with cannabinoid CB2 receptor antagonistic activities.

Uses

4,5-Imidazoledicarboxylic acid is an imidazole used for research purposes.

Synthesis

General procedure: 800 ml of concentrated sulfuric acid (80% concentration) was slowly added to 200 ml of water to form a reaction system. To this system was added 50.0 g of 2-propylbenzimidazole, followed by the slow dropwise addition of 30 mL of hydrogen peroxide to 500 mL of the reaction mixture. The reaction is exothermic and causes reflux, and the rate of titration needs to be controlled to maintain the reaction solution at a boil. After completion of the reaction, stirring was continued for 3 hours. Subsequently, 1000 mL of water was added to the reaction mixture and cooled to room temperature. The mixture was stirred for 3 hours at 0 to 5°C to promote precipitation of solids. The solid was collected by filtration and washed sequentially with water and 5% aqueous sodium sulfite solution (100 mL). The resulting solid was purified by column chromatography using water: methanol = 2:1 as eluent to give the final imidazole-4,5-dicarboxylic acid 3-lg with a melting point of 267.3 °C (simultaneous decomposition).

References

[1] Patent: CN104262260, 2016, B. Location in patent: Paragraph 0093-0095

4,5-Imidazoledicarboxylic acid(570-22-9)Related Product Information

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